Structure-activity relationship study of novel quinazoline-based 1,6-naphthyridinones as MET inhibitors with potent antitumor efficacy

Eur J Med Chem. 2020 Dec 15:208:112785. doi: 10.1016/j.ejmech.2020.112785. Epub 2020 Aug 31.

Abstract

As a privileged scaffold, the quinazoline ring is widely used in the development of EGFR inhibitors, while few quinazoline-based MET inhibitors are reported. In our ongoing efforts to develop new MET-targeted anticancer drug candidates, a series of quinazoline-based 1,6-naphthyridinone derivatives were designed, synthesized, and evaluated for their biological activities. The preliminary SARs studies indicate that the quinazoline scaffold was also acceptable for the block A of class II MET inhibitors. The further pharmacokinetic studies led to the identification of the most promising compound 22a with favorable in vitro potency (MET, IC50 = 9.0 nM), human microsomal metabolic stability (t1/2 = 621.2 min) and oral bioavailability (F = 42%). Moreover, 22a displayed good in vivo antitumor efficacy (IR of 81% in 75 mg/kg) in MET-positive human glioblastoma U-87 MG xenograft model. These positive results indicated that 22a is a potential new MET-targeted antitumor drug lead, which is worthy of further development.

Keywords: 1,6-naphthyridone; Antitumor; MET kinase Inhibitor; Quinazoline; Structure-activity relationship.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / therapeutic use*
  • Female
  • Glioblastoma / drug therapy*
  • Humans
  • Mice, Nude
  • Microsomes, Liver / metabolism
  • Molecular Docking Simulation
  • Molecular Structure
  • Naphthyridines / chemical synthesis
  • Naphthyridines / metabolism
  • Naphthyridines / therapeutic use*
  • Protein Binding
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / metabolism
  • Protein Kinase Inhibitors / therapeutic use*
  • Proto-Oncogene Proteins c-met / antagonists & inhibitors*
  • Proto-Oncogene Proteins c-met / metabolism
  • Quinazolines / chemical synthesis
  • Quinazolines / metabolism
  • Quinazolines / therapeutic use*
  • Rats
  • Structure-Activity Relationship
  • Thermodynamics
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Naphthyridines
  • Protein Kinase Inhibitors
  • Quinazolines
  • Proto-Oncogene Proteins c-met